Sodium Hydroxide → Dihydrocholesterol

HRID 1721305ノート

反応式

HRID 1721305 の反応式
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.CO>[CH3:26][CH:24]([CH2:23][CH2:22][CH2:21][C@H:20]([C@@H:19]1[C@:28]2([CH3:36])[C@H:16]([C@H:15]3[C@H:31]([CH2:30][CH2:29]2)[C@:32]2([CH3:35])[C@H:12]([CH2:11][C@@H:10]([OH:9])[CH2:34][CH2:33]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1)[CH3:27])[CH3:25]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 251110Cholestanol benzoate

生成物 1

HCID 6665Dihydrocholesterol収率 76%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of pyridazine 12 (113 mg, 0.22 mmol) in THF (1 mL) and MeOH (2 mL) was treated with 1M NaOH (0.29 mL, 0.29 mmol) and allowed to stand at ambient temperature for 16 h. The solvent was evaporated at reduced pressure and the residue was treated with CH2Cl2 (50 mL) and a 10% Na2CO3 solution (20 mL). The organic layer was separated, dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by flash chromatography on 4 g of silica gel 60 using MeOH/CHCl3 (5:95) giving 65 mg (72%) of 13, which crystallized from CH2Cl2 /acetone, mp 203°-205° C. 1H NMR: δ3.71 (m, 1H), 3.13 (dd, 1H, J=5.6, 13.4 Hz), 3.10 (dd, 1H, J=6.8, 16.5 Hz), 2.95 (dd, 1H, J=10.6, 16.3 Hz), 2.61 (dd, 1H, J=12.8, 17.9 Hz), 2.27 (dd, 1H, J=6.1, 11.0 Hz), 2.23 (ddd, 1H, J=3.6, 3.6, 13.4 Hz), 1.06 (s, 3H), 0.99 (d, 3H, J=6.2 Hz), 0.89 (d, 6H, J=6.6 Hz), 0.80 (s, 3H). IR (Nujol): 3301, 1626, 1554, 1035 cm-1. EIMS (m/z): 410 (M+), 395 (M-Me). Anal. (C27H42N2O): C, H, N.

後処理

  1. customThe solvent was evaporated at reduced pressure
  2. additionthe residue was treated with CH2Cl2 (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on 4 g of silica gel 60 using MeOH/CHCl3 (5:95)

出典と根拠

ORDレコード
ord-897d3c4b38d14067be4826b8f6627324
出典データセット
uspto-grants-1996_04
特許番号
US05510340

反応ノート

読み込み中…